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The Entrepreneur’s Step-by-Step Guide to Getting Ready to Make Your First Hire

April 20, 2022

Hiring a team as an entrepreneur is an exciting adventure, but how do you get ready to make your first hire? 

Maybe you’re wondering if you have what it takes to lead, or, maybe you’re worried about skipping a crucial step in the process and dealing with those repercussions later on. Perhaps deeper than that, you’re focused on making sure you’re taking the right steps for your company and the growth of your small business. 

The journey to making your first hire as a small business owner doesn’t have to be complicated, but it should be pursued with strategy, intention and time. 

Growth is good, but it’s your responsibility to make sure you provide the right structure, opportunity and direction to support your expansion and incoming hires, especially when hiring your first team member. 

In this guide to hiring your first team member, we will cover everything you need to do to prepare for making your first hire for your small or online business, including:

  • Structuring your internal business operations,
  • Structuring your team atmosphere and experience,
  • And, structuring your hiring process.  

When Is the Best Time to Make Your First Hire for Your Small Business?

Before diving into preparations for your first hire, it’s important to map out an appropriate timeline for bringing on your first and subsequent team members. 

Importantly, it’s better to give yourself more time to prepare for and lead the hiring process than less time. It’s better to plan for 3-6 or more months to prepare and execute your hiring strategy than to rush into it. 

Many entrepreneurs fall into a cycle of need and desperation without a hiring strategy and plan. Because they aren’t thinking far enough ahead, they wait to think about hiring until they feel a desperate, pressing need. They wait until their work-life balance is so out of whack they can no longer support their business themselves. They need help, and they needed help yesterday. Because of this, they rush into the hiring process, allowing that desperation to cloud their vision, discernment and intentionality. 

With a hiring process and strategy, you can avoid this trap – but it takes time. As a general rule, you can expect to spend one month or more preparing your hiring strategy and getting your operations ready (if they aren’t in order already).

After that, you can expect to spend a month or more launching, advertising, and reviewing applications. Then, the interviewing process with its 2-3 stages can take a month or longer, depending on the number of applicants and interviewing steps. You can expect to have someone selected and begin onboarding between 3 and 6 months. 

Getting Your Small Business Ready to Make Your First Hire

Now, let’s start getting ready to make your first hire and begin building a team for your small business! You’ll need to focus on creating structure in three key areas:

  1. Your business operations and workflows (aka, how your business runs)
  2. Your team culture and experience (aka, how your team runs)
  3. Your hiring and onboarding process (aka, how your recruitment runs)

Structuring Your Internal Business Operations & Workflows

Your first step is to get clear on your business structure and to solidify your model, offerings, products, and services. 

If these aren’t crystal clear, then the foundation on which you build your team will be shaky at best. Like many businesses with ambiguous structural models, you’ll end up shifting the roles of team members, establishing unclear lines of communication and responsibility, and will lack accountability and clear performance indicators. 

Getting clear on your business model is straightforward, but sometimes difficult, especially if you label yourself as a multi-passionate entrepreneur. It simply takes commitment to a product or offering and a process that your target audience will pay for. 

You’ll need to get clear on what you offer, who your audience is, who your competitors are, your value proposition, and do a bit of market research

Creating Standard Operating Procedures

To help you structure your internal operations, you’ll need to determine your core offers and cement your processes, creating Standard Operating Procedures – or, SOPs. 

Of course, you aren’t necessarily locking into this one way of doing things for the rest of your business life, but you are putting as much structure to the way you are currently doing things as you can. From here, you and your team can continually audit your processes and make tweaks to ensure efficiency and effectiveness as you grow. 

Determining What Team Member to Hire First

Knowing what role to fill first begins with looking at your company, no matter how large or small, as an organization with three clear and basic departments – marketing, fulfillment, and administration (or, operations). 

As a solo entrepreneur, you’re likely filling in all of those roles. You’re the marketing department, the online business manager, the program manager and client experience coordinator. 

Your task when preparing your business for bringing on your first team member is to highlight to most advantageous opportunity to build a new role. Here are a few helpful steps to guide you in that decision:

  1. Start with a time audit. As you prepare for expanding your team, let’s first audit your current actions. Take a workweek and track your tasks and time meticulously. We want to get an accurate picture of what actions you’re taking, if they’re profitable, and begin to see your current organizational structure take a shape. 
  2. Map your organizational structure. Once you complete your time audit, you’ll begin to shape up your organizational structure. Organize your tasks and projects by department and by process. For example, all content creation workflows fall under the ‘Marketing Department,’ all client processes fall under the ‘Fulfillment or Operations Department,’ and tasks like bookkeeping fall under the ‘Administrative Department.’
  3. Identify the role you want a team member to fill. Is there a current department, or process within that department you can hire someone to manage and work within? Where will you shift your focus next? What does growth look like for the team member you bring on? (Example: Is there room for them to grow from social media manager to marketing manager over time?)

Structuring Your Team Culture & Experience

Next, it’s time to add the heartbeat to your organization. You’ve got the structure – let’s give it some life. We do that with two different things, vision and core values. Let’s look at each: 


Vision is simply a compelling picture representing a beneficial future reality. It’s a picture of what can be – IF. It creates motivation, which stirs passion, which begets creativity, which awakens innovation – which drives change. 

Vision is that first domino in a line of dominos. It challenges people to achieve more, apply more of themselves, develop their strengths and get creative and work together. It’s the lifeblood of your team. 

To exist and be functional, a vision needs to evoke a picture. It needs to explain what the end goal is – what are we working toward? How will we know when we get there? What will it be like when we are successful in creating this new reality? What will it FEEL like? What about this future reality makes it SO special that I have to get out of my comfort zone and apply myself?

Core Values

Now that you understand your vision for your team and your company, what collective core values will help propel your team toward those heights? Core values not only help your team understand what right action looks like on your team, when lived out core values help align your daily actions to the path forward.

Core values are the bridge that communicates your vision, your purpose and your standards you require your team to uphold. Here are some helpful questions to work through as you begin to identify your own core values:

  • What is most important to you in your life? If you had to simplify living down to three simple truths to live by, what would they be?
  • What are some values that you practice each and every day? 
  • What people inspire you the most, and which of their qualities do you think attract you to them?
  • These things reflect your own internal core values, which are radiated into the teams that you lead. How so? How do these things translate into your team, your leadership and your business? 

After you journal, go back through what you’ve written and look for connecting themes. What thoughts, words, phrases or emotions repeatedly show up on the page? Now, can you begin to identify your core values?

Crafting Your Hiring Timeline

Now you’re ready to put legs to your hiring strategy and put some dates on your calendar! Your hiring process should include the following steps, however, the process is customizable. 

Step One, the Application Process

Applicants should send in their resumes and/or complete an application. You can expect to allot around a month to this process if you want to make sure you’re moving intentionally. You want to make sure you give yourself enough time to widely market the job posting. If you need help crafting a job posting that does its job, check out this podcast episode and resource here

Step Two, the Screening Process

Once you have a good amount of initial applications, you’ll begin the screening process. Through this process, you’re filtering out hard ‘No’s,’ or applicants that you know right off the bat aren’t a good fit. All the candidates that are ‘Maybe’s’ or ‘Yes’s’ can move forward in the screening process with a phone interview or project. You’ll filter their responses and move the ‘Yes’s’ forward. 

Step Three, the Formal Interview

You’ll move the ‘Yes’ candidates from the screening process onto the first formal interview. During these 20-30 minute interviews your goal is to experience initial connection and ask proficiency-focused questions. 

Step Four, the Informal Interview

Those who excel in the formal interview will move on to the next stage of the interview process. The purpose of the informal interview is to connect over vision, explore vulnerability, and map desired growth and action they would take if they filled the role. While I don’t recommend hosting any less than two interviews – an informal and formal – you may opt to add a third meeting or coffee date in there to help facilitate your decision. It’s up to you! 

Step Five, the Personality Fit Interview

A lot of people may want to fit personality screenings into their application process – I highly discourage doing so. Personality tests are not completely reliable – any ‘wrong’ or ‘off’ answer could distort the results entirely. This could cause you to miss out on a best fit hire or bring on someone who is entirely wrong for the team.

Instead, if you want to fit personality into your interview process, I suggest conducting a Personality Fit Interview. This is a fun interview step, where you have a peer, relative or close friend ‘interview’ your top candidate and give you their honest feedback on how they see this person’s personality and work style fitting with yours. 

(Disclaimer: Just because you don’t ‘click’ with someone who is otherwise a perfect fit for your team, that doesn’t mean you shouldn’t hire them.) As a leader, you should be building a diverse team with a diverse array of personalities. Your job isn’t to mesh on a personal level perfectly with all of your employees – your job is to hire the best people for the work who exemplify your core values and have a personality that will add perspective and depth to your team. 

If you want to have your top candidate take a personality test like the DiSC, Myers-Briggs or StrengthsFinders, have them do so as a final step – not for screening purposes, but for exploration purposes. Better yet, weave it into your onboarding process so you and your current team members can get to know your new hire even better. 

Step Six, Communicating the News

As much as you are able, give a verbal offer first. Verbal offers have higher acceptance rates than written offers. They’re also a great way to show your excitement. 

When communicating a verbal offer, here are some tips:

  • Share your excitement! You want them on your team for a reason. Now is your time to share openly why they stood out above the rest.
  • Share what you see in them. Speak life into this role you two will create together (should they accept!) Tell them what strengths you see in them and what skills you know will increase the impact of your company. 
  • Share the details. What is their pay? And, when would you like them to start work? 
  • Hear their answer. Hopefully, they say yes! Typically, candidates will request a period of time to discuss the offer with their partner and decide. Let them know they can take their time, but you would prefer an answer within 48 hours.
  • Thank them, and let them know you are here to answer any questions, any time. And for the next 48 hours, be available to answer the phone.

Step Seven, Telling the Others

Take a lesson from me, and don’t do what I did during my first hiring process – turn down the other applicants BEFORE I received a verbal and written acceptance from the woman I offered the position to.

She turned it down. And I had already turned away the rest. 

My second go-around? I waited until she SAID yes, and then I told the other applicants the news. Then… she said, “actually… nevermind.”

Don’t do what I did. Instead, wait until your new hire has SIGNED their contract, then email your other candidates and let them know. Thank them for their time, energy, and patience and ask them if they’d like for you to keep their resume on hand for future openings!

Now your business is ready for making your first hire. You have a sound internal structure with SOPs and processes, clear core values and vision for your team, and you have a hiring timeline planned and ready. 

Your next step? Craft a job posting that sells, and put together a 90-day onboarding plan to set your team member up for true success!

I'm Kaylan, leadership educator, podcaster & speaker

What are you searching for?

Reading suggestions

Crafting a 90-Day Onboarding Plan

Job Postings that Attract Top Talent

Mapping Your Leadership Style